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This article engages with history as a speculative space for the purpose of critically engaging with discourses around the politics of technology in HCI. Drawing on approaches within critical design and based on evidence from two different projects, we develop an approach, counterfactual actions , that moves beyond the creation of artifacts and towards more situated, embodied, and performative engagements. In one project, Reimaging Work, we used a participatory game to engage stakeholders from social and economic justice organizations in Chicago. The other project, Future Design Studio, invited audience members at a futurist festival to create artifacts from the future and then invited improvisational actors to build worlds around them. We argue that a focus on counterfactual actions supports a more relational approach to understanding the politics of socio-technical systems and infrastructures, allowing participants to gain a meaningful understanding of the ways in which technology could be designed otherwise in line with ethics, values and social justice concerns.